Identification

Name
Caprylic acid
Accession Number
DB04519  (EXPT02413)
Type
Small Molecule
Groups
Experimental, Investigational
Description

Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid-like smell that is minimally soluble in water.

Structure
Thumb
Synonyms
  • capryloate
  • Caprylsaeure
  • Enantic acid
  • Kaprylsaeure
  • n-caprylic acid
  • n-octanoic acid
  • n-Octoic acid
  • n-octylic acid
  • neo-fat 8
  • octanoate
  • octanoic acid
  • Octic acid
  • octoic acid
  • Octylic acid
External IDs
EDENOR C 8-98-100 / FEMA NO. 2799 / NSC-5024
Categories
UNII
OBL58JN025
CAS number
124-07-2
Weight
Average: 144.2114
Monoisotopic: 144.115029756
Chemical Formula
C8H16O2
InChI Key
WWZKQHOCKIZLMA-UHFFFAOYSA-N
InChI
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
IUPAC Name
octanoic acid
SMILES
CCCCCCCC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 1Not AvailableEscherichia coli (strain K12)
UAcyl-CoA thioesterase INot AvailableEscherichia coli (strain K12)
UPeroxisome proliferator-activated receptor alphaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral rat LD50: 10080 mg/kg. Intravenous mouse LD50: 600 mg/kg. Skin rabbit LD50: over 5000 mg/kg.

Affected organisms
Not Available
Pathways
PathwayCategory
Fatty Acid BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

William Elliott Bay, Joseph Norman Bernadino, George Frederick Klein, Yi Ren, Pingsheng Zhang, "METHODS FOR PRODUCING N-(8-[2-HYDROXYBENZOYL]-AMINO) CAPRYLIC ACID." U.S. Patent US20080064890, issued March 13, 2008.

US20080064890
General References
Not Available
External Links
Human Metabolome Database
HMDB00482
KEGG Drug
D05220
KEGG Compound
C06423
PubChem Compound
379
PubChem Substance
46507647
ChemSpider
370
ChEBI
28837
ChEMBL
CHEMBL324846
HET
OCA
Wikipedia
Caprylic_acid
PDB Entries
1h2b / 1u8u / 1v2g / 2bui / 2eum / 2qhs / 2wg9 / 3l91 / 3nq9 / 3wl8
show 9 more
MSDS
Download (78.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentTremor, Essential1
1, 2CompletedTreatmentEssential Tremor of Voice / Essential Voice Tremor / Vocal Tremor / Voice Tremor1
1, 2CompletedTreatmentTremor, Essential1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)16.3 °CPhysProp
boiling point (°C)239 °CPhysProp
water solubility789 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.05HANSCH,C ET AL. (1995)
pKa4.89 (at 25 °C)DEAN,JA (1987)
Predicted Properties
PropertyValueSource
Water Solubility0.907 mg/mLALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m3·mol-1ChemAxon
Polarizability17.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9888
Blood Brain Barrier+0.9488
Caco-2 permeable+0.8326
P-glycoprotein substrateNon-substrate0.6321
P-glycoprotein inhibitor INon-inhibitor0.9598
P-glycoprotein inhibitor IINon-inhibitor0.9277
Renal organic cation transporterNon-inhibitor0.9266
CYP450 2C9 substrateNon-substrate0.7886
CYP450 2D6 substrateNon-substrate0.8956
CYP450 3A4 substrateNon-substrate0.6982
CYP450 1A2 substrateInhibitor0.8326
CYP450 2C9 inhibitorNon-inhibitor0.8808
CYP450 2D6 inhibitorNon-inhibitor0.9554
CYP450 2C19 inhibitorNon-inhibitor0.9578
CYP450 3A4 inhibitorNon-inhibitor0.9484
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9865
CarcinogenicityNon-carcinogens0.6452
BiodegradationReady biodegradable0.8795
Rat acute toxicity1.3275 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9322
hERG inhibition (predictor II)Non-inhibitor0.8868
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0159-0910000000-e609d5de69ede6fbcde0
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0gb9-1920000000-1dc6ed976e003f99e23d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03kc-9000000000-74cfce03769b41313952
GC-MS Spectrum - EI-BGC-MSsplash10-0uyi-0931100000-7668e36e436054042b5c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0910000000-e609d5de69ede6fbcde0
GC-MS Spectrum - GC-MSGC-MSsplash10-0gb9-1920000000-1dc6ed976e003f99e23d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0910000000-9ecb4ccb46e89710f76a
Mass Spectrum (Electron Ionization)MSsplash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0006-0900000000-bb237630bedcee6145d1
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-2900000000-98284f50a271878c8481
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-5900000000-209fbbacd4996b9a770d
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-03kc-9000000000-74cfce03769b41313952
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0006-0900000000-e2c4dff10393086340f7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-1900000000-bbde8564b4e5543a636a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Q-Exactive Plus , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0900000000-e2c4dff10393086340f7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-1900000000-bbde8564b4e5543a636a
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0006-0900000000-ca22ecd0b25fa371fc73
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Medium-chain fatty acid / Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
medium-chain fatty acid, straight-chain saturated fatty acid (CHEBI:28837) / Straight chain fatty acids, Saturated fatty acids (C06423) / Straight chain fatty acids (LMFA01010008)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
3-oxoacyl-[acyl-carrier-protein] synthase activity
Specific Function
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Specific for elongation from C-10 to unsaturated C-16 and C-18 fatty...
Gene Name
fabB
Uniprot ID
P0A953
Uniprot Name
3-oxoacyl-[acyl-carrier-protein] synthase 1
Molecular Weight
42612.995 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Phospholipase activity
Specific Function
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin.
Gene Name
tesA
Uniprot ID
P0ADA1
Uniprot Name
Acyl-CoA thioesterase I
Molecular Weight
23621.955 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ: Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci. 2006 Aug;92(2):476-89. Epub 2006 May 26. [PubMed:16731579]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456]
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:43